Detailed Information on Publication Record
2003
Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters
LITERÁK, Jaromír, Stanislav RELICH, Petr KULHÁNEK and Petr KLÁNBasic information
Original name
Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters
Authors
LITERÁK, Jaromír (203 Czech Republic), Stanislav RELICH (203 Czech Republic), Petr KULHÁNEK (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor)
Edition
Molecular Diversity, Basel, Switzerland, Kluwer, 2003, 1381-1991
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Field of Study
10401 Organic chemistry
Country of publisher
Switzerland
Confidentiality degree
není předmětem státního či obchodního tajemství
Impact factor
Impact factor: 4.444 in 2001
RIV identification code
RIV/00216224:14310/03:00008279
Organization unit
Faculty of Science
UT WoS
000207200600021
Keywords in English
photochemistry; microwave; protecting groups
Tags
International impact
Změněno: 9/2/2007 14:21, prof. RNDr. Petr Klán, Ph.D.
Abstract
V originále
The study of the temperature-sensitive photochemical release of a carboxylic acid from 2,5-dimethylphenacyl ester is reported. Quantum yields of the benzoate ester degradation in benzene increased from 0.22 at room temperature to 0.28 at 50 oC whereas a more significant increase (nearly by a factor of 3) was observed in methanol and ethanol, reaching a high reaction efficiency (0.25) typically found in non-polar solvents. The reaction proceeds predominantly via the triplet pathway and the E-photoenol in the whole temperature range in methanol solution. A higher quantum efficiency in heated methanol is explained by enhancing the E-photoenol population. This picture was partially confirmed by the quantum chemical calculations. The 2,5-dimethylphenacyl chromophore is proposed as an efficient photoremovable protecting group for carboxylic acids in solutions under conventional or microwave-assisted heating for applications in organic synthesis, such as the solid-phase synthesis.
Links
GA203/02/0879, research and development project |
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MSM 143100005, plan (intention) |
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